Benzamidopyrimidines



United States Patent 3,317,534 BENZAMIDOPYRIMIDINES Yoshihiro Nitta, Tokyo, Fumio Yoneda, Chigasaki-shi, and Toshio Miyamoto, Tokyo, Japan, assignors to Chugai Seiyaku Kabushiki Kaisha, Tokyo, Japan No Drawing. Filed Sept. 25, 1964, Ser. No. 399,341 Claims priority, application Japan, Oct. 30, 1963, 38/57,518 7 Claims. (Cl. 260-2564) R1 N NHCORa (I) wherein R stands for lower alkoxy radical or di-lower alkylamino radical, R stands for lower alkoxy radical, di-lower alkylamino radical or chloro radical, R does not indicate neither lower alkoxy radical nor di-lower alkylamino radical different from R in case R stands for lower alkoxy radical and R does not indicate neither lower alkoxy radical nor di-lower alkylamino radical diflferent from R in case R stand-s for di-lower alkylamino radical and R stands for phenyl radical or phenyl radical having one or more of same radicals or of diiferent radicals selected from the group'consisting of lower alkoxy radical, hydroxy radical, lower alkyl radical, nitro radical and halogeno radical as substituent.

According to the present invention, the compounds represented by the general Formula I may be produced by reacting aminopyrimidines represented by the general formula:

XCOR (III) wherein X stands for halogen atom and R stands for the same meaning as mentioned above.

In the practice of the present invention it is preferable to react in the presence of basic substance For the basic substance, for example, alkali carbonate, triethylamine, triethanoamine, pyridine, quinoline and the like may be employed. Further the reaction isadvisable to be done in a solvent such as benzene, toluene, Xylene, dioxane, dimethylformamide, pyridine and the like. Pyridine is most advantageously used because of the property of the starting materials being easy soluble in it and being basic substance. In case pyridine is used the reaction proceeds well at room temperature but it proceeds more rapidly by heating.

The new benzamidopyrimidines (I) produced by the present process are useful as antibacterial substance and are eiiective for gram-positive and gram-negative bacteria. Further the compound (I) having nitro radical is effective for Mycobacterium tuberculosis =var. Izominis and is useful as chemotherapeutic agent.

The results obtained by the investigation of the antibacterial activity of new benzamidopyrimidines in nitro for Staphylococcus aureus, Shigella flexneri, Proteus vulgasis, Mycobacterium tuberculosis, Trichophyton mentagrophytes, Candida albicans is shown in the following Table 1, sulfadirnethoxine, isoniazid, bithionol being used as controls.

TABLE 1 R NHCORa Benzamidopyrirnidines Bacteria Staph. .S'hz'g.flex., Pr.vulg., M. tubem, T. manta Galvin, R1 R2 R3 aureus, mcgJml. meg/ml. meg/ml. meg/ml. meg/ml.

meg/ml.

--OM1 OM1 o1 6. 2-12. 5 6. 2 6. 2

()Me ()M 25 25 12. 5

0Me OMe -o1 12.5 25 12.5

OMe -OMe 20 0 TABLE ll-Continned Benzamidopyrimidines Bacteria Staph. Shz'g. flex Pr. vulg., M. tubem, T. menta., C. alvic., R1 R2 R aureus, mcgJml. mcg./ml. mcg./m1. mcg./m1. mcgJml.

mcg./ml.

IYIO: -nBu -0nBu 2. 2. 5 2. 5 5 2. 5 2. 5

OMe C1 Q01 5- 5 5 5 5 5 0 Me C1 20 20 20 20 20 -OMe -Cl 20 20 20 20 Me Me -N N\ 12 5 12. 5 12. 5

Me Me (ll Me Me N N\ C1 12 5 12. 5 12. 5

Me Me a 01 /Me /Me N\ N\ 10 10 6. 2

Me Me Me N Cl Cl 10 20 125 Me -N\ -Cl 10 10 6. 2

Me --N\ Ol OMe 6.2 6.2 12. 5

Sulfadirnethoxine 1. 25-2. 5 1. 25-2. 5 20 Isoniazid 0.1 Bithionol 0 6 10 The present invention will be explained more in detail by Way of examples.

Example 1' 1.6 g. of 4-amino-2,G-dirnethoxypyrimidine and 1.6 g.

.of 2-hydroxybenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon, 2.1 g. of 4-(2-hydroxybenzamido)-2,6-dimethoxypyrimidine is obtained, M.P. 204 C.

Elementary analysis as C H O N -Calc. (percent):

C, 56.72; H, 4.76; N, 15.21.

Found percent: C, 57.04; H, 4.77; N, 15.53.

Example 3 I The crystal resulted from the treatment of 3.1 g. of

4-amino-2,6-dimethoxypyrimidine and 3.1 g. of Z-methyl- Elemental analysis as C H O N -Calc. (percent): C,

61.53; H, 5.53; N, 15.38. 5.74; N, 15.43.

Found (percent): C, 61.92; H,

Example 4 The crystal resulted from the treatment of 3.1 g. of 4- amino-2,6-dimethoxypyrimidine and 3.1 g. of B-methyl- 4 benzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute ethanol, whereupon 42 g. of 4-(3-methylbenzamido)-2,6-dimethoxypyrimidine is obtained, M.P. 122 C.

Elemental analysis as C H O N -Calc. (percent) C, 61.53; H, 5.53; N, 15.38. Found (percent): C, 61.34; H, 5.55; N, 15.44.

Example 5 The crystal resulted from the treatment of 3.1 g. of 4-arnino-2,6-dimethoxypyrimidine and 3.1 g. of 4-methylbenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 4.5 g. of 4-(4-methylbenzamido)-2,6-dimethoxypyrimidine is obtained, M.P. 137 C.

Elemental analysis as C H O N Calc. (percent): C, 61.53; H, 5.53; N, 15.38. Found (percent): C, 61.34; H, 5.30; N, 15.59.

Example 6 The crystal resulted from the treatment of 3.1 g. of 4- a-mino-2,6-dimethoxypyrimidine and 3.5 g. of 2-chlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute ethanol, whereupon 5.1 g. of 4-(2-chlorobenzamido)-2,6-dimethoxypyrimidine is obtained, M.P. 126 C.

Elemental analysis as C H O N ClCalc. (percent): C, 53.16; H, 4.12; N, 14.38. Found (percent): C, 53.35; H, 4.14; N, 14.20.

Example 7 The crystal resulted from the treatment of 3.1 g. of 4-amino-2,6-dimethoxypyrimidine and 3.5 g. of 4-chlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from ethanol, whereupon 5.8 g. of 4-(4-chlorobenzamido)-2,6-dimethoxypyrimidine is obtained, M.P. 155 C.

Element analysis as C H O N ClCalc. (percent): C, 53.16; H, 4.12; N, 14.38. Found (percent): C, 53.37; H, 4.15; N, 14.25.

Example 8 The crystal resulted from the treatment of 3.1 g. of 4-amino-2,6-dimethoxypyrirnidine and 4.4 of 3-bromobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute ethanol, whereuon 6.5 g. of 4-(3-bromohenzamido)-2,6-dimethoxypyrimidine is obtained, M.P. 93 C.

Elemental analysis as C H O N BrCalc. (percent): C, 43.84; H, 3.97; N, 11.80. Found (percent): C, 43.83; H, 3.80; N, 11.53.

Example 9 The crystal resulted from the treatment of 1.6 g. of 4-amino-2,6-dimethoxypyrimidine and 2.1 g. of 3,4-dichlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 2.6 g. of 4-(3,4-dichlorobenzamido)-2,6-dimethoxypyrimidine is obtained, M.P. 158 C.

Elementary analysis as C H O N Cl Calc. percent: C,47.58; H, 3.38; N, 12.81. Found (percent): C, 47.40; H, 3.39; N, 12.81.

Example The crystal resulted from the treatment of 3.1 g. of 4-amino-2,6-dimethoxypyrimidine and 4.2 g. of 2,4-dichlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 6.0 g. of 4-(2,4-dichlor-obenzamido)-2,6-dimeethoxypyrimidine is obtained, M.P. 145 C.

Elemental analysis as C H O N Cl Cals. (percent) C, 47.58; H, 3.38; N, 12.81. Found (percent): C, 47.72; H, 3.40; N, 12.78.

Example 11 The crystal resulted from the treatment of 3.1 g. of 4-amino-2,6-dirnethoxypyrimidine and 3.4 g. of 4-methoxybenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol,

8 whereupon 5.1 g. of 4-(4-methoxybenzamido)-2,6-dimethoxy'pyrimidine is obtained, M.P. 143 C.

Elemental analysis as C H O N Calc. (percent): C, 58.12; H, 5.23; N, 14.53. Found (percent): C, 57.93; H, 5.07; N, 14.52.

Example 12 The crystal resulted from the treatment of 3.1 g. of 4- amino-2,6-di-methoxypyrimidine and 4.0 g. of 3,4-dimethoxybenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 5.3 g. of 4-(3,4-dimethoxybenzamido)- 2,6-dimethoxypyrimidine is obtained, M.P. 167 C.

Elemental analysis as C H O N -Ca1c. (percent): C, 56.42; H, 5.37; N, 13.16. Found (percent): C, 56.61; H, 5.42; N, 13.15.

Example 13 The crystal resulted from the treatment of 3.1 g. of 4-a-rnino-2,6-dimethoxy-pyrimidine and 4.6 g. of 3,4,5-trimethoxybenzoyl chloride in the same manner as in EX- ample 1 is subjected to recrystallization from dilute methanol, whereupon 6.1 g. of 4-(3,4,5-trimethoxybenzamido) 2,6-di-methoxypyrimidine is obtained, MJP. 107 C.

Elemental analysis as C H 'O N Calc. (percent): C, 55.01; H, 5.48; N, 12.03. Found (percent): C, 54.94; H, 5.64; N, 11.91.

Example 14 The crystal resulted from the treatment of 3.1 g. of 4-amino-2,6-dimethoxypyri-midine and 3.7 g. of 4-nitrobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from methanol, whereupon 5.1 g. of 4-(4-nitrobenzamido)-2,6-dimethoxypyrimidine is obtained, M.P. 184 C.

Elemental analysis as C H O N Calc. (percent): C, 51.31; H, 3.98; N, 18.42. Found (percent): C, 51.15; H, 4.16; N, 18.27.

Example 16 The crystal resulted from the treatment of 3.1 g. of 4- amino-2,6-dimethoxypyrimidine and 4.6 g. of 3,5-dinitrobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 6.2 g. of 4-(3,5-dinitrobenzamido)-2,6-dimethoxypyrimidine is obtained, M.P. 177 C.

Elemental analysis as C H O N Calc. (percent): C, 44.70; H, 3.17; N, 20.05. Found (percent): C, 44.91; H, 3.31; N, 20.02.

Example 17 The crystal resulted from the treatment of 3.1 g. of 4-amino-2,6-dimethoxypyrimidine and 4.4 g. of 3-nitro-4- chlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from methanol, whereupon 6.2 g. of 4-(3-nitro-4chlorobenzamido)-2,6- dimethoxypyrimidine is obtained, M.P. 185 C.

Elemental analysis as C H O N ClCalc. (percent): C, 46.10; H, 3.27; N, 16.54. Found (percent): C, 46.04; H, 3.47; N, 16.69.

Example 18 1.6 g. of 4-amino-2,6-dimethoxy pyrimidine and 1. 8 g. of 3-chloro-benzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.4 g. of 4-(3-chlorobenzamido)-2,6-dimethoxypyrimidine is obtained, M.P. 108 C.

9 Elemental analysis as C H O N 'ClCalc. percent): C, 53.16; H, 4.12; N,'14.38. Found (percent): C, 52.80; H, 4.35; N, 14.20.

Example 19 1.6 g. of 4-amino-2,6-dimethoxypyrimidine and 2.2 g. of 4-bromobenzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.8 g. of 4-(4-'bromobenzamido)-2,S-dimethoxypyrimidine is obtained, M.P. 151 C.

. Elemental analysis as C H O N BrCalc. (percent): C, 46.17; H, 3.58; N, 12.43. Found (percent): C, 46.27; H, 3.63; N, 12.69.

Example The crystal resulted from the treatment of 3.7 g. of 4-amino-2,6-diethoxypyrimidine and 2.8 g. of benzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute ethanol, whereupon 5.0 g. of 4 benzamido-2,6-diethoxypyri-midine having one molecule of water of crystallization is obtained, M.P. 76 C.

Elemental analysis as C H O N Calc. (percent): C, 59.00; H, 6.27; N, 13.76. Found (percent): C, 59.24; H, 6.51; N, 13.91.

Example 21 The crystal resulted from the treatment of 1.8 g. of 4-amino-2,6-diethoxypyrimidine and 1.6 g. of Z-hydroxybenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 2.5 g. of 4-(2-'hydroxybenzamido)-2,6-diethoxypyrimidine is obtained, M.P. 178 C.

Elemental analysis as C H O N Calc. (percent): C, 59.39; H, 5.65; N, 13.86. Found (percent): C, 59.68; H, 5.69; N, 13.70.

Example 22 The crystal resulted from the treatment of 3.7 g. of 4- amino-2,6-diethoxypy-rimidine and 3.1 g. of 2-methylbenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute ethanol, where upon 5.2 g. of 4-(Z-methylbenzamide)-2,6-diethoxypyrimidine is obtained, M.P. 108 C.

Elemental analysis as C H O N -Calo (percent): C, 63.77; H, 6.36; N, 13.95. Found (percent): C, 63.61; H, 6.54; N, 13.87.

Example 23 is subjected to recrystallization from dilute methanol,'

whereupon 5.0 g. of 4-(4-methylbenzamide)-2,6-diethoxypyrimidine is obtained, M.P. 128 C.

Elemental analysis as C H O N Calc. (percent): C, 63.77; H, 6.36; N, 13.95. Found (percent): C, 63.88; H, 6.45; N, 14.05.

Example 25 Ehe crystal resulted from the treatment of 3.7 g. of 4- amino-2,6-diethoxypyrimidine and 3.5 g. of 2-chlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute ethanol, whereupon 5.8 g. of 4-(2-chlorobenzamide)-2,6-diethoxypyrim idine is obtained, M.P. 98 C.

Elemental analysis as C H O N ClCalc. (percent):

10 C, 55.99; H, 5.01; N, 12.88. Found (percent): C, 56.15; H, 4.82; N, 12.65:

Example 26 The crystal resulted from the treatment of 3.7 g. of 4- amino-Z,6-diethoxypyrimidine and 3.5 g. of 4*chlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute ethanol, whereupon 6.0 g. of 4-(4-chlorobenzamide)-2,6-diethoxypyrimidine is obtained, M.P. C.

Elemental analysis as C H O N Cl-Calc. (percent): C, 55.99; H, 5.01; N, 13.06. Found (percent): C, 56.21; H, 4.88; N, 12.75.

Example 27 The crystal resulted from the treatment of 1.8 g. of 4- amino-2,6-diethoxypyrimidine and 2.1 g. of 3,4-dichlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute ethanol, whereupon 3.0 g. of 4-(3,4-dichlorobenzamide)-2,6-diethoxypyrimidine is obtained, M.P. 141 C.

Elemental analysis as C H O N Cl Calc. (percent): C, 50.58; H, 4.24; N, 11.80. Found (percent): C, 50.61; H, 4.30; N, 11.91.

Example 28 The crystal resulted from the treatment of 3.7 g. of 4- amino-2,6-diethoxypyrimidine and 4.2 g. of 2,4-dichlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute ethanol, whereupon 6.5 g. of 4-(2,4-dichlorobenzamide)-2,6-diethoxypyrimidine is obtained, M.P. 116 C.

Elemental analysis as C H O N Cl -Calc. (percent): C, 50.58; H, 4.24; N, 11.80. Found (percent): C, 50.41; H, 4.19; N, 11.78.

Example 29 The crystal resulted from the treatment of 1.8 g. of 4- amino-2,6-diethoxypyrimidine and 3.1 g. of 2-hydroxy- 3,5-dibromobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 3.2 g. of 4-(2-hydroxy-3-5-dibromobenzamide)-2,6-diethyl pyrimidine is obtained, M.P. 166 C.

Elemental analysis as C H O N Br Calc. (percent): C, 39.07; H, 3.28; N, 9.11. Found (percent): C, 39.16; H, 3.35; N, 8.90.

Example 30 The crystal resulted from the treatment of 3.7 g. of 4- amino-2,6-diethoxypyrimidine and 3.4 g. of 4-methoxybenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, 'whereupon 5.5 g. Y of 4-(4-metl1oxybenzamide)2,6-diethoxypyrimidine is obtained, M.P. 116 C.

Elemental analysis as C H O N Calc. (percent): C, 60.55; H, 6.04; N, 13.24. Found (percent): C, 60.87; H, 5.76; N, 12.96.

Example 31 The crystals resulted from the treatment of 3.7 g. of 4-amin0-2,6-diethoxypyrimidine and 3.7 g. of 3-nitrobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 5.4 g. of 4-(3-nitrobenzamide)-2,6-diethoxypyridine is obtained, M.P. 113 C.

Elemental analysis as C H O N Calc. (percent): C, 54.21; H, 4.85; N, 16.86. Found (percent): C, 54.14; H, 4.63; N, 16.82.

Example 32 The crystal resulted from the treatment of 3.7 g. of 4- amino-2,6-diethoxypyrimidine and.3.7 g. of 4-nitrobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from methanol, whereupon 5.9 g. of 4-(4-nitrobenzamide)-2,6-diethoxypyrirnidine is obtained, M.P. 159 C.

1 1 Elemental analysis as C H O N Calc. (percent): C, 54.21; H, 4.85; N, 16.86. Found (percent): C, 54.43; H, 4.94; N, 17.00.

Example 33 The crystal resulted from the treatment of 3.7 g. of 4- amino-2,6-diethoxypyrimidine and 4.6 g. of 3,5-dinitrobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 5.8 g. of 4-(3,5-dinitro'benzamide)-2,6-diethoxypyrimidine is obtained, M.P. 170 C.

Elemental analysis as C H O N Calc. (percent): C, 47.75; H, 4.01; N, 18.56. Found (percent): C, 47.94; H, 4.06; N, 18.72.

Example 34 The crystal resulted from the treatment of 3.7 g. of 4- amino-2,6-diethoxypyrimidine and 4.4 g. of 3-nitro-4- chlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from methanol, whereupon 6.2 g. of 4-(3-nitro-4-chlorobenzamide)-2,6-diethoxypyrimidine is obtained, M.P. 151 C.

Elemental analysis as C H O N ClCalc. (percent): C, 49.12; H, 4.12; N, 15.28. Found (percent): C, 49.11; H, 3.98; N, 14.99.

Example 35 1.8 g. of 4-amino-2,6-diethoxypyrimidine and 2.2 g. of 4-bromobenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from of 4-(4-bromobenzamido)-2,6-diethoxypyrimidine is obtained, M.P. 129 C.

Elemental analysis as C H O N Br-Calc. (percent): C, 49.20; H, 4.40; N, 11.47. Found (percent): C, 49.23; H, 4.36; N, 11.25.

Example 36 The crystal resulted from the treatment of 1.6 g. of 2-methoxy-4-amino-6-chloropyrimidine and 1.4 g. of benzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 2.1 g. of 2-methoxy-4-benzamide-6-chloropyrimidine is obtained, M.P. 109 C.

Elemental analysis as C H O N Cl-Calc. (percent): C, 54.64; H, 3.96; N, 15.94. Found (percent): C, 54.67; H, 3.85; N, 15.82.

Example 37 The crystal resulted from the treatment of 1.6 g. of 2- rrtethoxy-4-amino-6-chloropyrimidine and 1.5 g. of 2- methylbenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute ethanol, whereupon 2.0 g. of 2-methoxy-4-(2-methylbenzamide)-6-chloropyrimidine is obtained, M.P. 117 C.

Elemental analysis as C H O N ClCalc. (percent): C, 56.23;H, 4.36; N, 15.13. Found (percent): C, 56.16; H, 4.4-2; N, 15.11.

Example 38 The crystal resulted from the treatment of 1.6 g. of 2-methoxy-4-amino-6-chloropyrimidine and 1.5 g. of 4- methylbenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 1.9 g. of 2-methoxy-4-(4-methylbenzamide)- 6-chloropyrimidine is obtained, M.P. 185 C.

Elemental analysis as C H O N Cl-Calc. (percent):

dilute methanol, whereupon 2.9 g.

12 C, 56.23; H, 4.36; N, 15.13. Found (percent): C, 56.40; H, 4.62;N, 15.28.

Example 40 The crystal resulted from the treatment of 1.6 g. of 2- methoxy-4-amino-6-chloropyrimidine and 1.8 g. of 2- chlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute ethanol, whereupon 2.4 g. of 2-methoxy-4-(2-chlorobenzamide)- 6-chloropyrirnidine is obtained, M.P. 136 C.

Elemental analysis as C H O N Cl -Calc. (percent): C, 48.34; H, 3.04; N, 14.10. Found (percent): C, 48.53; H, 3.09; N, 14.05.

Example 41 The crystal resulted from the treatment of 1.6 g. of 2-methoxy-4-amino-6-chloropyrimidine and 1.8 g. of 4- chlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute ethanol, whereupon 2.5 g. of 2-methoxy-4-(4-chlorobenzamide- 6-chloropyrimidine is obtained, M.P. 198 C.

Elemental analysis as C H O N Cl Calc. (percent): C, 48.34; H, 3.04; N, 14.10. Found (percent): C, 48.54;

Example 42 The crystal resulted from the treatment of 1.6 g. of 2-methoxy-4-amino-6-chloropyrimidine and 2.1 g. of 2,4- dichlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 2.3 g. of 2-methoxy-4-(2,4 dichlorobenz-amide)-6-chloropyrimidine is obtained, M.P. 146 C.

Elemental analysis as C H O N Cl Calc. (percent): C, 43.40; H, 2.42; N, 12.64. Found (percent): C, 43.03;

Example 43 The crystal resulted from the treatment of 1.6 g. of 2-methoxy-4-amino-6-chloropyrimidine and 1.9 g. of 4- nitrobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from glacial acetic acid, whereupon 2.2 g. of 2-meth0xy-4-(4-nitrobenzamide)-6- chloropyrimidine is obtained, M.P. 225 .5 C.

Elemental analysis as C H O N Cl-Calc. (percent): C, 46.69; H, 2.94; N, 18.15. Found (percent): C, 46.55; H, 2.90; N, 18.01.

Example 44 The crystal resulted from the treatment of 1.6 g. of 2-methoxy-4-amino-6-chloropyrimidine and 2.2 g. of 3- nitro-4-chlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallized from methanol, whereupon 2.4 g. of 2-methoxy-4-(3-nitro-4-chlorobenzamide)-6-chloropyrimidine is obtained, M.P. 159 C.

Elemental analysis as C H O N Cl Calc. (percent): C, 42.00; H, 2.35; N, 16.33. Found (percent): C, 42.11; H, 2.04; N, 16.24.

Example 45 1.6 g. of 4-amino-2-methoxy-6-chloropyrimidine and 2.1 g. of 3,4-dichlorobenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.6 g. of 4-(3,4-dichlorobenzamido)-2-methoxy-6-chloropyrimidine is obtained, M.P. C.

Elemental analysis as C H O N Cl -Calc. (percent): C, 43.40; H, 2.42; N, 12.64. Found (percent): C, 43.27; H, 2.38; N, 12.67.

Example 46 1.6 g. of 4-amin0-2-methoxy-6-chloropyrimidine and 2.2 g. of 4-bromobenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.0 g. 4-(4-bromobenzamido)-2-me-thoxy-6-chloropyrimidine is obtained, M.P. 202 C.

Elemental analysis as C H O N ClBrCalc. (percent): C, 42.07; H, 2.65; N, 12.27. Found (percent): C, 42.15; H, 2.58; N, 12.09.

13 Example 47 1.6 g. of 4-amino-2-methoxy-6-chloropyrimidine and 2.2 g. of 3-bromobenzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.1 g. of 4-(3-bromobenzamido)-2 methoxy 6- chloropyrimidine is obtained, M.P. 111 C.

Elemental analysis as C H O N ClBr-Calc. cent): C, 42.07; H, 2.65; N, C, 42.28; H, 2.51; N, 12.38.

Example 48 1.7 g. of 3-amino-2-ethoxy-6-ch1oropyrimidine and 1.8 g. of 4-chlorobenzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.4 g. of 4-(4-chlorobenzamido)-2-ethoxy-6-chloropyrimidine is obtained, M.P. 126 C.

Elemental analysis as C H O N Cl Calc. (percent): C, 50.02; H, 3.55; N, 13.46. Found (percent): C, 50.09; H, 3.45; N, 13.70.

(p 12.27. Found (percent) Example 49 1.7 g. of 4-amino-2-ethoxy-6-chloropyrimidine and 2.1 g. of 3,4-dichlorobenzoyl chloride is treated in the same manners as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.5 g. of 4-(3,4-dichlorobenzami'do)-2-ethoxy- 6-chloropyrirnidine is obtained, M.P. 146 C.

Elemental analysis as C H O N Cl Calc. (percent): C, 45.05; H, 2.91; N, 12.12. Found (percent): C, 45.42; H, 3.21; N, 11.90.

Example 50 1.7 g. of 4-amino-2-ethoxy-fi-chloropyrimidine and 2.2 g. of 4-bromobenzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.4 g. of 4-(4-bromobenzamido)-2-ethoxy-6-chloropyrimidine is obtained, M.P. 123 C.

Elemental analysis as C H O N ClBrCalc. (percent): C, 43.79; H, 3.11; N, 11.78. Found (percent): C, 44.05; H, 3.13; N, 11.65.

Example 51 1.7 g. of 4-amino-2-ethoxy-6-chloropyrimidine and 2.2 g. of 3-bromobenzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.6 g. of 4-(3-bromobenzamido)-2-ethoxy-6-chloropyrimidine is obtained, M.P. 116 C.

Elemental analysis as C H O N ClBrCa1c. (percent): C, 43.79; H, 3.11; N, 11.78. Found (percent): C, 43.98; H, 3.16; N, 11.51.

Example 52 1.7 g. of 4-amino-2-ethoxy-G-chloropyrimidine and 2.1 g. of 2,4-dichlorobenzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.3 g. of 4-(2,4-dichlorobenzamido)-2-ethoxy-6- chloropyrimidine is obtained, M.P. 92 C.

Elemental analysis as C H O N Cl -Calc (percent): C, 45.05; H, 2.91; N, 12.12. Found (percent): C, 44.85; H, 3.04; N, 11.74.

Example 53 1.7 g. of 4-amino-2-ethoxy-6-chloropyrimidine and 1.5 g. of 4-methylbenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.2 g. of 4-(4-rnethy1benzamido)-2-ethoxy-6-chlo ropyrirnidine is obtained, M.P. 106 C.

Elemental analysis as C H O N C1Calc. (percent): C, 57.64; H, 4.84; N, 14.40. Found (percent): C, 57.69; H, 4.77; N, 14.70.

1 4 Example 54 1.7 g. of 4-amino-2-ethoxy-6-chloropyrimidine and 1.8 g. of 2-chlorobenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 25 g. of 4-(2-chlorobenzamido)-2-ethoxy-6-chloropyrimidine is obtained, M.P. 137 C.

Elemental analysis as C H O N Cl Calc. (percent): C, 50.02; H, 3.55; N, 13.46. Found (percent): C, 50.25; H, 3.49; N, 13.52.

Example 55 subjected to recrystallization from dilute methanol, whereupon 2.1 g. of 2-n-propoxy-4-benzamide-6-chloropyrimidine is obtained, M.P. 86 C.

Elemental analysis as C H O N Cl-Calc. (percent): C, 57.63; H, 4.83; N, 14.45. Found (percent): C, 57.57; H, 4.92; N, 14.22.

Example 57 The crystal resulted from the treatment of 1.9 g. of 2-n-propoxy-4-amino-6-chloropyrimidine and 1.8 g. of 2- chlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 2.2 g. of 2-n-propoxy-4-(2-chlorobenzamide)- 6-chloropyrimidine is obtained, M.P. 122 C.

Elemental analysis as C H O N Cl Ca1c. (percent): l

C, 51.55; H, 4.02; N, 12.88. Found (percent): C, 51.71; H, 4.10; N, 12.85.

Example 58 The crystal resulted from the treated of 1.9 g. of 2-npropoxy-4-amino-6-chloropyrimidine and 1.8 g. of 4-chlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 2.6 g. of 2-n-propoxy-4-(4-chlorobenzamide)- 6-chloropyrimidine is obtained, M.P. 112 C.

Elemental analysis as C H O N C-lCa1c. (percent): C, 51.55; H, 4.02; N, 12.88. Found (percent): C, 51.65; H, 3.97; N, 12.85.

Example 59 The crystal resulted from the treatment of 1.9 g. of 2-n-propoxy-4-amino-6-ch1oropyrimidine and 1.9 g. of 4- nitrobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from methanol, whereupon 2.3 g. of 2-n-propoxy-4-(4-nitrobenzamide)-6-chl0ropyrimidine is obtained, M.P. 168 C.

Elemental analysis as C H O N ClCalc. (percent): C, 49.93; H, 3.88; N, 16.64. Found (percent): C, 50.27; H, 3.89; N, 16.76.

Example 60 1.9 g. of 2-n-propoxy-4-amino-6-chloropyrimidine and 2.1 g. of 3,4-dichlorobenz-oyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.5 g. of 2-n-propoxy-4-(3,4-dichlorobenzamido)-6-ch1oropyrirnidine is obtained, M.P. 128 C.

Elemental analysis as C H O N Cl Calc. (percent): C, 46.64; H, 3.35; N, 11.65. Found (percent): C, 46.77; H, 3.23; N, 11.34.

Example 61 1.9 g. of 2-n-propoxy-4-amino-6-chloropyrimidine and 2.2 g. of 4-bromobenzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.9 g. of 2-n-propoxy-4-(4-bromobenzamido)-6- chloropyrimidine is obtained, M.P. 107 C.

Elemental analysis as C H O N Cll3r-Calc. (percent): C, 45.37; H, 3.54; N, 11.34. Found (percent): C, 45.25; H, 3.37; N, 1130.

Example 62 1.9 g. of 2-n-propoxy-4-amino-6-chloropyrimidine and 1.5 g. of 4-methylbenzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.5 g. of 2-n-propoxy-4-(4-methylbenzamido)-6- chloropyrimidine is obtained, M.P. 115 C.

Elemental analysis as C H O N ClCalc. (percent): C, 58.92; H, 5.27; N, 13.74. Found (percent): C, 58.61; H, 5.23; N, 13.38.

Example 63 1.9 g. of 2-n-propoxy-4-amino-chloropyrimidine and 2.3 g. of 3,5-dinitrobenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2,8 g. of 2-n-propoxy-4-(3,5-dimethylbenzamido)- 6-chl0ropyrimidine is obtained, M.P. 143 C.

Elemental analysis as C H O N Cl-Calc. (percent): C, 44.05; H, 3.17; N, 18.35. Found (percent): C, 44,42; H, 3.34; N, 18.07.

Example 64 1.9 g. of 2-i-propoxy-4-amino-6-chloropyrimidine and 1.4 g. of benzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.3 g. of 2-i-propoxy-4-benzarnido-6-chloropyrimidine is obtained, M.P. 142 C.

Elemental analysis as C H O N ClCalc. (percent): C, 57.64; H, 4.84; N, 14.40. Found (percent): C, 57.51; H, 4.56; N, 14.31.

Example 65 1.9 g. of 2-i-propoxy-4-amino-6-chloropyrimidine and 1.8 g. of 4-chlorobenzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.4 g. of 2-i-propoxy-4-(2-chlorobenzamido)-6- ropyrimidine is obtained, M.P. 133 C.

Elemental analysis as C H O N C-l Calc. (percent) C, 51.55; H, 4.02; N, 12.88. Found (percent): C, 51.72; H, 3.86; N, 12.98.

Example 66 1.9 g. of 2-i-propoxy-4-amin0-6-chloropyrimidine and 2.1 g. of 3,4-dichlorobenzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained .is subjected to recrystallization from dilute methanol,

whereupon 2.6 g. of 2-i-propoxy-4-(3,4-dichlorobenzamido)-6-chloropyrimidine is obtained, M.P. 140 C.

Elemental analysis as C H O N Cl Calc. (percent) C, 46.63; H, 3.35; N, 11.65. Found (percent): C, 46.83; H, 3.31; N, 11.70.

Example 68 g. of 2-i-propoxy-4-amino-6-chloropyrimidine and g. of 4-bromobenzoylcl1loride is treated in the same manner as in Example 1. The crystal thus Obtained is subjected to recrystallization from dilute methanol, whereupon 2.9 g. of 2-i-propoxy-4-(4bromobenzamido)-6- chloropyrimidine is obtained, M.P. 150 C.

Elemental analysis as C H O N ClBr-Calc. (percent): C, 45.37; H, 3.54; N, 11.34. Found (percent): C, 45.65; H, 3.59; N, 11.53.

Example 69 1.9 g. of 2-i-propoxy-4-amino-6-chloropyrimidine and 1.5 g. of 4-methylbenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.3 g. of 2-i-propoxy-4-(4-methylbenzamido)-6- chloropyrimidine is obtained, M.P. 131 C.

Elemental analysis as C H O N Cl-Cale (percent): C, 58.92; H, 5.27; N, 13.74. Found (percent): C, 58.63; H, 5.22; N. 13.79.

Example 70 1.9 g. of Z-i-propoxy-4-amino-6-chloropyrimidine and 2.3 g. of 3,5-dinitrobenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.6 g. of 2-iropoxy-4-(3,5-dinitrobenzamido)-6- chloropyrimidine is obtained, M.P. 181 C.

Elemental analysis as C H O N Cl-Calc. (percent): C, 44.05; H, 3.17; N. 18.35. Found (percent): C, 43.77; H, 3.23; N, 18.45.

Example 71 The crystal resulted from the treatment of 2.1 g. of 4- amino-2,6-di-n-propoxypyrimidine and 1.8 g. of 4-chlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 2.6 g. of 4-(4-chlorobenzamide)-2,6-di-n-propoxypyrimidine is obtained, M.P. 84 C.

Elemental analysis as C H O N Cl-Calc. (percent): C, 58.37; H, 5.76; N, 12.01. Found (percent): C, 58.46; H, 5.53; N, 12.13.

Example 72 2.1 g. of 4-amino-2,6-di-n-propoxypyrimidine and 2.3 g. of 3,5-dinitrobenzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.7 g. of 4-(3,5-dinitrobenzamido)-2,6-di-n-propoxypyrimidine is obtained, M.P. 108 C.

Elemental analysis as C H O N Calc. (percent): C, 50.37; H, 4.72; N, 17.28. Found (percent): C, 50.68; H, 4.67; N, 17.32.

Example 73 2.1 g. of 4-amino-2,6-di-n-propoxypyrimidine and 2.2 g. of 4-bromobenzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.5 g. of 4-(4-bromobenzamido)-2,6-di-n-propoxypyrimidine is obtained, M.P. 79 C.

Elemental analysis as C H O N BrCalc. (percent): C, 51.79; H, 5.11; N, 10.66. Found (percent): C, 51.76; H, 5.42; N, 10.47.

Example 74 2.1 g. of 4-amino-2,6-di-n-propoxypyrimidine and 2.1 g. of 3,4-dichlorobenzoylchloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.4 g. of 4-(3,4-dichlorobenzamido)-2,6-di-npropoxy'pyrimidine is obtained, M.P. 86 C.

Elemental analysis as C H O N Cl Calc. (percent): C, 53.14; H, 4.98; N, 10.94. Found (percent): C, 53.15; H, 5.06; N, 11.00.

Example 75 2.1 g. of 4-amino-2,6-di-n-propoxypyrimidine and 1.5 g. of 4-methylbenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, Where- 1 7 upon 2.9 g. of 4-(4-methyl-benzamido)-2,6-di-n-propoxypyrimidine is obtained, M.P. 78 C.

Elemental analysis as C H O N Ca1c. (percent): C, 65.63; H, 7.04; N, 12.76. Found (percent): C, 65.39; H, 6.97; N, 12.70.

Example 76 The crystal resulted from the treatment of 2.1 g. of 4-amino-2,6-di-i-propoxypyrimidine and 1.8 g. of 4-chlorobenzoyl chloride in the same manner as in Example 1 is subjected to recrystallization from dilute methanol, whereupon 2.7 g. of 4-(4-chlorobenzamide)-2,6-di-i-propoxypyrimidine is obtained, M.P. 102 C.

Elemental analysis as C H O N ClCalc. (percent): C, 42.58; H, 3.02; N, 22.94. Found: (percent): C, 42.36; H, 2.91; N, 22.76. i

Y Example 77 The crystal resulted from the treatment of 2.2 g. of 4-amino-2,6-di-i-propoxypyrimidine and 2.3 g. of 3,5-dinitrobenzoylchloride in the same manner as in Example 1 is subjected to recrystallization from dilute ethanol, whereupon 3.5 g. of 4-(3,5-dinitrobenzamide)-2,6-di-ipropoxypyrimidine is obtained, M.P. 176 C.

Elemental analysis as C H O N Oalc. (percent): C, 50.37; H, 4.72; N, 17.28. Found (percent): C, 50.41; H, 5.08; N, 17.19.

Example 78 2.1 g. of 4-amino-2,6-di-i-propoxypyrimidine and 2 g. of 4-bromobenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.5 g. of 4-(4-bromobenzamido)-2,6-di-i-propoxypyrimid-ine is obtained, M.P. 145 C.

Elemental analysis as C H O N BrCalc. (percent):

0, 51.79; H, 5.11; N, 10.66. Found (percent): C. 52.03;

Example 79 2.1 g. of 4-am'ino-2,6-di-i-propoxypyrimidine and 2.1 g. of 3,4-dichlorobenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.4 g. of 4-(3,4-dichlorobenzamido)-2,6-di-ipropoxypyrimidine is obtained, M.P. 111 C.

Elemental analysis as C H O N Cl Calc.

(percent): C, 53.14; H, 4.98; N, 10.94.

Found (percent: C,

Example 80 2.1 g. of 4-amino-2,6-di-i-propoxypyrimidine and 2.1 g.

of 2,4-dichlorobenzoyl chloride is treated in the same -manner as in Example 1.

The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.3 g. of4-(2,4-dichloro-benzamido)-2,6-di-ipropoxypyrimidine is obtained, M.P. 120 C.

Elemental analysis as C H O N Cl Calc. (percent): C, 53.14; H, 4.98; N, 10.94. Found (percent): C,

Example 81 2.1 g. of 4-amino-2,G-di-i-propoxypyrimidine and 1.5 g. of 4-methylbenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.8 g. of 4-(4-methylbenzamido)-2,6-di-i-propoxypyrimidine is obtained, M.P. 96 C.

Elemental analysis as C H O N Calc. (percent): C, 65.63; H, 7.04; N, 12.76. Found (percent): C. 65.92; H, 7.19; N, 12.64.

- Example 82 2.4 g. of 4-an1ino-2,6-di-n-butoxypyrimidine and 2.3 g. of 3,5-dinitrobenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from isopropylether, whereupon 3.4 g. of 4-(3,5-dinitrobenzamido)-3,6-di-n-butoxypyrimidine is obtained, M.P. 115 C.

18 Elemental analysis as C H O N -Ca1e (percent); C, 52.65; H, 5.35; N, 16.16. Found (percent): C, 52.89; H, 5.36; N, 16.15.

Example 83 2.4 g. of 4-amino-2,6-di-n-butoxypyrimidine and 1.8- g. of 4-chlorobenzoyl chloride is treated in the same inanner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.2 g. of 4-(4-chlorobenzamido)-2,6-di-n-butoxypyrimidine is obtained, M.P. 71 C.

Elemental analysis as C H O N Cl Calc. (percent): C, 60.39; H, 6.40; N, 11.12. Found (percent): C, 60.09; H, 6.47; N, 11.20.

Example 84 2.4 g. of 4-amino-2,6.-di-n-butoxypyrimidine and 2.1 g. of 3,4-dichlorobenzoyl chloride is treated in the same manner as in Example The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.5 g. of 4-(3,4-dichlorobenzamido) -2,6-di-n-butoxypyrimidine is obtained, M.P. 89 C.

Elemental analysis as C H O N Cl -Calc; (percent): C, 55.35; H, 5.62; N, 10.19. Found (percent): C, 55.53; H, 5.72; N, 9.89.

Example 85 2.4 g. of 4-amino-2,6-di-n-butoxypyrimidine and 2.2 g. of 4-bromobenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.7 g. of 4-(4-bromobenzamido)-2,6-di-n-butoxypyrimidine is obtained, M.P. C.

Elemental analysis as C H O N BrCalc. (percent): C, 54.04; H, 5.73; N, 9.95. Found (percent): C, 54.18; H, 5.89; N, 9.73.

Example 86 2.4 g. of 4-amino-2,6-di-i-butoxypyrimidine and 2.3 g. of 3,5-dinitrobenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from isopropylether, whereupon 3.5 g. of 4-(3,5-dinitrobenzamido)-2,6,-di-i-butoxypyrimidine is obtained, M.P. 109 C.

Elemental analysis as C H O N Calc. (percent): C, 52.65; H, 5.35; N, 16.16. Found (percent): C, 52.85; H, 5.40; N, 16.42.

Example 87 2.4 g. of 4-amino-2,6-di-i-butoxypyrimidine and 1.6 g. of 4-chlorobenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.3 g. of 4-(4-chlorobenzamido)-2,6-di-i-butoxypyrimidine is obtained, M.P. 134 C.

Elemental analysis as C H O N Cl-Calc. (Percent): C, 60.39; H, 6.40; N, 11.12. Found (percent): C, 60.00; H, 6.45; N, 11.01.

Example 88 2.4 g. of 4-amino-2,6-di-i-butoxypyrimidine and 2.2 g. of 4-bromobenzoyl chloride is treated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.6 g. of 4-(4-bromobenzamido)-2,6di-i-butoxypyrimidine is obtained, M.P. 101 C.

Elemental analysis as C H O N BrCalc. (percent):

C, 54.04; H, 5.73; N, 9.95. Found (percent): C, 54.16; H, 5.85; N, 9.57.

Example 90 2.4 g. of 4-amino-2,6-di-i-butoxypyrimidine and 1.5 g. of 4-methylbenzoyl chloride is trated in the same manner as in Example 1. The crystal thus obtained is subjected to recrystallization from isopropylether, whereupon 3.1 g. of 4-(4-methylbenzamido)-2,6-di-i-butoxypyrimidine is obtained, M.P. 129 C.

Elemental analysis as C2oH27O3N3-C2HC, (percent): C, 67.20; H, 7.61; N, 11.76. Found (percent): C, 67.22; H, 7.74; N, 11.52.

Example 91 1.8 g. of 4-amino-2,6-bis-(dimethylamino)-pyrimidine is dissolved in 15 ml. of anhydrous pyridine. To the solution 1.5 g. of 2-methylbenzoyl chloride is added little by little in dropwise under cooling and shaking, whereby the reaction complete at once and the reaction mixture solidify. After left to stand overnight, the crystal deposited by addition of 50 ml. of water under stirring is collected by filtration and washed with water. Recrystallization from dilute ethanol give 2.0 g. of 4-(2-methylbenzamide)- 2,6-bis-(dimethylamino)-pyrimidine, M.P. 136.5 C.

Elemental analysis as C H ON -Calc. (percent): C, 64.19; H, 7.07; N, 23.40. Found (percent): C, 64.47; H, 7.07; N, 23.60.

Example 92 The crystal resulted from the treatment of 1.8 g. of 4-amino-2,6-bis-(dimethylamino)-pyrimidine and 1.5 g. of 3-methylbenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from methanol, whereupon 2.1 g. of 4-(3-methylbenzamide)-2,6-bis-(dimethylamino)-pyrimidine is obtained, M.P. 131 C.

Elemental analysis as C H ON Calc. (percent): C, 64.19; H, 7.07; N, 23.40. Found (percent): C, 63.89; H, 7.06; N, 23.73.

Example 93 The crystal resulted from the treatment of 1.8 g. of 4-amino-2,6-bis-(dimethylamino)-pyrimidine and 1.5 g. of 4-methylbenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from methanol, whereupon 2.2 g. of 4-(4-methylbenzarnide)-2,6-bis-(dimethylamino)-pyrimidine is obtained, M.P. 176.

Elemental analysis as C H ON Calc. (percent): C, 64.19; H, 7.07; N, 23.40. Found (percent): C, 63.95; H, 7.03; N, 23.59.

Example 94 The crystal resulted from the treatment of 1.8 g. of 4-amino-2,6-bis-(dimethylamino)-pyrimidine and 1.8 g. of Z-chlorobenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from dilute ethanol, whereupon 2.3 g. of 4-(2-chlorobenzarnide)-2,6- bis-(dimethylamino)-pyrimidine is obtained, M.P. 136 C.

Elemental analysis as C H O N BrCalc. (percent): C, 56.33; H, 5.63; N, 21.90. Found (percent): C, 56.13; H, 5.64; N, 21.54.

Example 95 The crystal resulted from the treatment of 1.8 g. of 4- amino-2,6-bis-(dimethylamino)-pyrimidine and 2.2 g. of 3-bromobenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from dilute ethanol, whereupon 2.4 g. of 4-(3-bromobenzamide)-2,6-bis- (dimethylamino)pyrimidine is obtained, M.P. 98 C.

Elemental analysis as C H O N BrCalc. (percent): C, 47.01; H, 5.27; N, 18.32. Found (percent): C. 46.51; H, 5.26; N, 17.97.

Example 96 The crystal resulted from the treatment of 1.8 g. of 4- amino-2,6-bis-(dimethylamino)-pyrimidine and 1.7 g. of 4-met-hoxybenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from dilute methanol, whereupon 2.0 g. of 4-(4-methoxybenzamide)- 20 2,6-bis-(dimethylamino)-pyrimidine is obtained, M.P. 154 C.

Elemental analysis as C H O N Calc. (percent): C, 60.93; H, 6.71; N, 22.21. Found (percent): C, 60.86; H, 7.01; N, 22.35.

Example 97 The crystal resulted from the treatment of 1.8 g. of 4- amino-2,6-bis-(dimethylamino)-pyrimidine and 2.0 g. of 3,4-dimethoxybenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from dilute methanol, whereupon 2.2 g. of 4-(3,4-dimethoxybenzamide) 2,6 bis-(dimethylamino)-pyrimidine containing water of crystallization of one molecule is obtained, M.P. C.

lemental analysis as C H O N Calc. (percent) C, 56.18; H, 6.93; N, 19.27. Found (percent): C, 56.10; H, 6.72; N, 19.26.

Example 98 The crystal resulted from the treatment of 1.8 g. of 4- amino-2,6-bis-(dimethylamino)-pyrimidine and 2.3 g. of 3,4,S-trimethoxybenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from dilute methanol, whereupon 2.8 g. of 4-(3,4,5-trimethoxybenzamide) 2,6 bis-(dimethylamino)-pyrimidine containing water of crystallization of one molecule is obtained, M.P. 157 C.

Elemental analysis as C H O N -Calc. (percent): C, 54.95; H, 6.92; N, 17.80. Found (percent): C, 54.64; H, 6.94; N, 17.74.

Example 99 The crystal resulted from the treatment of 1.8 g. of 4- arnino-2,6-bis-(dimethylamino)-pyrimidine and 2.2 g. of 3-nitro-4-chlorobenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from methanol, whereupon 2.5 g. of 4-(3-nitro-4-chlorobenzamide)- 2,6-bis-(dimethylamino)-pyrimidine is obtained, M.P. 182 C.

Elemental analysis as C H O N -ClCalc. (percent): C, 49.38; H, 4.70; N, 23.04. Found (percent): C, 48.96; H, 4.73; N, 23.22.

Example 100 The crystal resulted from the treatment of 1.8 g. of 4- amino-2,6-bis-(dimethylamino)-pyrimidine and 2.3 g. of 3,5-dinitrobenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from ethanol, whereupon 2.5 g. of 4-(3,5-dinitrobenzamide)-2,6-bis-(d1- methylamino)-pyrimidine is obtained, M.P. 257 C.

Elemental analysis as C15H17O5N7CalC. (percent): C, 48.00; H, 4.57; N, 26.12. Found (percent): C, 47.86; H, 4.68; N, 26.03.

Example 101 The crystal resulted from the treatment of 1.7 g. of 2- dimethylamino-4-amino-6-chloropyrimidine and 1.5 g. of Z-methylbenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from ethanol, whereupon 2.3 g. of 2-dimethylamino-4-(2-methylbenzamide)-6-chloropyrimidine is obtained, M.P. 186 C.

Elemental analysis as C H ON Cl-Calc. (percent): C, 57.83; H, 5.20; N, 19.27. Found (percent): C, 57.95; H, 5.24; N, 19.51.

Example 102 The crystal resulted from the treatment of 1.7 g. of 2-dimethylamino-4-amino-6-chloropyrimidine and 1.5 g. of 3-methylbenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from methanol, whereupon 2.1 g. of 2-dirnethylarnino-4-(3-methylbenzamide)-6-chloropyrimidine is obtained, M.P. C.

Elemental analysis as C H ON ClCalc. (percent): C, 57.83; H, 5.20; N, 19.27. Found (percent): C, 57.69; H, 5.48; N, 19.30.

Example 103 The crystal resulted from the treatment of 1.7 g. of

21 2-dimethylamino-4-amino-6-chloropyrimidine and 1.5 g. of 4-methylbenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from methanol, whereupon 2.2 g. of 2-dimethylamino-4-(4-methylbenzamide)-6-chloropyrimidine is obtained, M.P. 160 C.

Elemental analysis as C H ON ClCalc. (percent): C, 57.83; H, 5.20; N, 19.27. Found (percent): C, 57.87; H, 5.38; N, 19.26.

Example 104 The crystal resulted from the treatment of 1.7 g. of 2-dimethylamino-4-amino-6-chloropyrimidine and 1.8 g. of 2-chlorobenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from methanol, whereupon 2.5 g. of 2-dimethylamino-4-(2-chlorobenzamide) 6 chloropyrimidine is obtained, M.P. 201.s c. g V

Elemental analysis as C H ON Cl Calc. (percent): C, 50.17; H, 3.89; N, 18.01. Found (percent): C, 50.41; H,.4.13; N, 17.90.

' Example 105 The crystal resulted from the treatment of 1.7 g. of 2-dimethylamino-4-amino-6-chloropyrimidine and 1.8 g. of 4-chlorobenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from dilute ethanol, whereupon 2.6 g. of 2-dimethylamino-4-(4- chlorobenzamide)-6-chloropyrimidine is obtained, M.P. 142.5 C.

Elemental analysis as C H ON Cl Calc. (percent): C, 50.17; H, 3.89; N, 18.01. Found (percent): C, 49.89; H, 4.08; N, 17.78.

Example 106 The crystal resulted from the treatment of 1.7 g. of

' 2-dimethylamino-4-amino-6-chloropyrimidine and 2.2 g.

of 3-bromobenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from methanol, whereupon 3.1 g. of 2-dimethylamino-4-(3-bromobenzamide)-6-chloropyrimidine is obtained, M.P.153" C. nol, whereupon 2.6 g. of 2-dimethy1amino-4-(4-methoxy- Elemental analysis as C H ON ClBr-Calc. (percent): C, 43.91; H, 3.40;,N, 15.76. Found (percent): C, 44.15; H, 3.17; N, 16.15.

Example 107 The crystal resulted from the treatment of 1.7 g. of 2-dimethylamino-4-amino-6-chloropyrimidine and 1.7 g. of 4-methoxybenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from methanol, whereupon 2.6g. of 2-diethylamino-4-(4-methoxy benzamide)-6 chloropyrimidine is obtained, M.P. 165 C.

Elemental analysis as C H O N ClCalc. (percent): C, 54.93; H, 4.93; N, 18.37. Found (percent): C, 55.00; H, 5.12; N, 18.09.

Example 108 The crystal resulted from the treatment of 1.7 g. of Z-dimethylamino-4-amino-6-chloropyrimidine and 2.2 g. of 3-nitro-4-chlorobenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from methanol, whereupon 3.0 g. of 2-dimethylamino-4-(3- nitro-4-chlorobenzamide)-6-chlor0pyrimidine is obtained, M.P. 193 C.

Elemental analysis as C H O N Cl Calc. (persame manner as in Example 91.

22 cent): C, 43.89; H, 3.11; N, 19.66. Found (percent): C, 43.96; H, 3.35; N, 19.36.

Example The crystal resulted from the treatment of 1.7 g. of 2-dimethylamino-4-amino-6-chloropyrimidine and 2.3 g. of 3,5-dinitr'obenzoyl chloride in the same manner as in Example 91 is subjected to recrystallization from dilute methanol, whereupon 2.7 g. of 2-dimethylamino-4-(3,5- dinitrobenzamide)-6-chloropyrimidine is obtained, M.P. 217 C.

Elemental analysis as C H O N ClCa1c. (percent): C, 58.37; H, 5.76; N, 12.01. Found (percent): C, 58.24; H, 5.64; N, 12.08.

Example 111 "1.7 g. of Z-dimethylamino-4-amino-6-chloropyrimidine and 1.4 g. of benzoyl chloride is treated in the same manner as in Example 91. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.2 g. of 2-dimethylamino-4-benzamido-6chloropyrimidine is obtained, M.P. 182 C.

Elemental analysis as C H ON ClCalc. (percent): C, 56.43; H, 4.76; N, 20.25. Found (percent): C, 56.41; H, 4.72; N, 20.35.

Example 112 1.7 g. of 2-dimethylamino-4-amino-6-chloropyrimidine and 2.1 g. of 3,4-dichlorobenzoyl chloride is treatedin the same manner as in Example 91. The crystal thus obtained is subjected to recrystallization from dilute ethanol, whereupon 2.8 g. of 2-dimethylamino-4-(3,4-di- -chlorobenzamido)-6chloropyrimidine is obtained, M.P.

Elemental analysis as C H ON Cl -Calc. (percent): C, 45.18; H, 3.21; N, 16.21. Found (percent): C, 45.52; H, 3.27; N, 16.16.

Example 113 1.7 g. of 2-dimethylamino-4-amin-o-6-chloropyrimidine and 1.8 g. of 3-chlorobenzoylchloride is treated in the The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.3 g. of 2-dimethylamino-4-(3-chlorobenzamido)-6-chloropyrimidine is obtained, M.P. 157 C.

Elemental analysis as C H ON Cl Calc. (percent): C, 50.17; H, 3.89; N, 18.01. Found (percent): C, 49.99; H, 4.15; N, 17.89.

Example 114 2.0 g. of 2-diethylamino-4-amino-6-chloropyrimidine and 1.4 g. of benzoyl chloride is treated in the same manner as in Example 91. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 2.4 g. of 2-diethy1amino-4-benzamido-6-chloropyrimidine is obtained, M.P. 138 C.

Elemental analysis as C H ON ClCalc. (percent): C, 59.11; H, 5.62; N, 18.38. Found (percent): C, 58.93; H, 5.61; N, 18.50.

Example 2.0 g. of 2-diethylamino-4-amino-6-chloropyrimidine and 1.8 g. of 4-chlorobenzoyl chloride is treated in the same manner as in Example 91. The crystal thus obtained is subjected to recrystallization from ethanol, whereupon 2.7 g. of 2-diethylamino-4-(4chlorobenzamido)-6-chloropyrimidine is obtained, M.P. 157 C.

Elemental analysis as C H ON Cl Calc. (percent): C, 53.11; H, 4.75; N, 16.52. Found (percent): C, 53.08; H, 4.67; N, 16.34.

Example 116 2.0 g. of 2-diethylamino-4-amino-6-chloropyrimidine and 1.8 g. of 2-chlorobenzoyl chloride is treated in the same manner as in Example 91. The crystal thus obtained is subjected to recrystallization from ethanol, whereupon 2.6 g. of 2-diethylamino4-(2-chlorobenzamido)-6-chloropyrimidine is obtained, M.P. 167 C 23 Elemental analysis as C H ON Cl -C,alc. (percent): C, 53.11; H, 4.75; N, 16.52. Found (percent): C, 52.81; H, 4.61; N, 16.47.

Example 117 2.0 g. of 2-diethylamino-4-amino-6-chloropyrimidine and 2.1 g. of 3,4-dichlorobenz-oyl chloride is treated in the same manner as in Example 91. The crystal thus obtained is subjected to recrystallization from methanol, whereupon 3.1 g. of 2-diethylamino-4-(3,4-dichlorobenzamido)-6-chloropyrimidine is obtained, M.P. 154 C.

Elemental analysis as C H ON Cl Calc. (percent): C, 48.22; H, 4.05; N, 14.99. Found (percent): C, 47.99; H, 4.16; N, 14.91.

Example 119 2.0 g. of 2-diethylarnino-4-amino-6chloropyrirnidine and 2.2 g. of 4-bromobenzoyl chloride is treated in the same manner as in Example 91. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.2 g. of 2-diethylamino-4-(4- :bromobenzamido)-6-chloropyrimidine is obtained, M.P. 159 C.

Elemental analysis as C H ON ClBrCa1c. (percent): C, 46.96; H, 4.20; N, 14.60. Found (percent): C, 47.01; H, 4.09; N, 14.67.

Example 120 2.0 g. of 2-diethyla-mino-4-amino-6-chloropyrimidine and 2.2 g. of 3-bromobenzoyl chloride is treated in the same manner as in Example 91. The crystal thus obtained is subjected to recrystallization from dilute methanol, whereupon 3.0 g. of 2-diethylarnino-4-(3- bromobenzamido)-6-chloropyrimidine is obtained, M.P. 111 C.

Elemental analysis as C H ON ClBrCalc. (percent): C, 46.96; H, 4.20; N, 14.60. Found (percent): C, 47.07; H, 4.48; N, 14.62.

Example 121 2.0 g. of 2-diethylamino-4-amino-6-cyclopyrimidine and 1.5 g. of 4-methylbenzoyl chloride is treated in the same manner as in Example 91. The crystal thus obtained is subjected to recrystallization from methanol, whereupon 2.7 g. of 2-diethylamino-4-(4-methylbenzamido-6-chloropyrimidine is obtained, M.P. 143 C.

Elemental analysis as C H ON ClCalc. (percent): C, 60.28; H, 6.01; N, 17.57. Found (percent): C, 60.37; H, 6.09; N, 17.27.

We claim: 1. 4-(4-chlorobenzamido)-2,6-dimethoxypyrimidine. 2. 4-(4-chlorobenzamido)-2,6-diethoxypyrimidine. 3. 4-(4-chlorobenzamido)-2,6-di-n-propoxypyrimidine. 4. 4-(3,4-dichlorobenzarnido)-2,6-diethoxypyrimidine. 5. A compound of the formula wherein R and R are each selected from the group consisting of alkoxy of less than five carbon atoms "and dialkylamino of less than five carbon atoms.

6. A compound according to claim 5, wherein R and R are both lower alkoxy.

7. A compound of the formula sq j NHCOR:

wherein R and R are each selected from the group consisting of .alkoxy of less than five carbon atoms and dialkylarnino of less than five carbon atoms; and R is selected from the group consisting of phenyl and (X),,- substituted phenyl, wherein X is selected from the group consisting of hydroxy and halo, and n is an integer less than 3.

References Cited by the Examiner UNITED STATES PATENTS 2,502,528 4/1950 Morf 260-2564 X 2,554,186 5/1951 Goldberg et a1. 260-2564 X 3,152,136 10/1964 Harris et a1 260256.4 X

OTHER REFERENCES Rose et 211.: Jour. Chem. Soc., 1946, pages 81-85.

ALEX MAZEL, Primary Examiner.

HENRY R. JILES, Examiner.

MARY U. OBRIEN, Assistant Examiner. 

7. A COMPOUND OF THE FORMULA 